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Author: Subject: How do you decide what you want to synthesize?
xeneficus
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[*] posted on 23-7-2016 at 00:45
How do you decide what you want to synthesize?


I'm a new initiate into the dark order of the erlenmeyer flask, so this might be obvious to those more experienced.

Looking at all of the syntheses in organic chemistry, it feels like 90% of the compounds don't have a specific function, as far as I can tell from a novice's standpoint. Inorganic chemistry has the sex appeal of high energy materials and precious metals; the goal is to make something that blows up or is shiny. In organic chemistry do you decide what to synthesize for its use? If so, where do you find new, interesting compounds to synthesize? Or is it just in the challenge of the reaction?
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Melgar
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[*] posted on 23-7-2016 at 08:49


I dunno, organic chemistry has had its own sex appeal ever since Breaking Bad became popular. Now I regularly have people ask me "do you know how to make meth as good as Walter White's in Breaking Bad?" Yes, it's an incredibly easy synthesis. In fact, Walter White was kind of an idiot for wasting so much energy trying to steal methylamine, when he could have just gotten nitromethane racing fuel by the bucket, and reduced it in a one-pot reductive amination. Also, what the fuck was that blue impurity? Nothing good, I'm sure.

Hell, tell most people that you can make methamphetamine by reductively aminating phenylacetone with methylamine, and they'll be impressed. "What's phenylacetone?" "Oh, you know acetone? Like nail polish remover? Like that, with a phenyl group attached to one side."

Note: do not actually make methamphetamine. Right now I'm actually trying to make dopamine via the Henry reaction, using caffeine as the base catalyst. None of it would be useful at all, but I'm not sure it's ever been done before and documented, and it seems a rather appropriate set of reactants.

[Edited on 7/23/16 by Melgar]
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[*] posted on 23-7-2016 at 09:12


A lot of people usualy have a goal molecule in mind, and will work toward that goal through a series of intermediates. Examples may include drugs (or inactive analogs thereof), dyes, acid/base indicators, fluorescent molecules, or natural products of various classes.

Sometimes a chemist will want to perform particular reactions that they have become interested in, and will gather the most convenient reagents to do so without any specific end product in mind. For example, if you wanted to try a Fisher esterifcation, you might use easily available ethanol and acetic acid to make ethyl acetate, or perhaps salicylic acid (from aspirin) and methanol to make methyl salicylate. And so on.

Also, some operate from the point of what is on hand, and seeing how many products they could make from a particular compound. Many OTC medications can serve as rich starting points. Quite a few products can be had from aspirin alone. Salicylic acid and its various esters, phenol, picric acid, salicylamide, 2-aminophenol, and on and on.
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[*] posted on 23-7-2016 at 09:18


Quote: Originally posted by Melgar  
Now I regularly have people ask me "do you know how to make meth as good as Walter White's in Breaking Bad?" Yes, it's an incredibly easy synthesis. In fact, Walter White was kind of an idiot for wasting so much energy trying to steal methylamine, when he could have just gotten nitromethane racing fuel by the bucket, and reduced it in a one-pot reductive amination. Also, what the fuck was that blue impurity? Nothing good, I'm sure.
[Edited on 7/23/16 by Melgar]


I get asked stuff like that a lot. My friends have asked me before "how's your meth lab doing" (I don't manufacture any drugs, they just hear about organic chemistry and jump to that :D). I also like the ability to tell people about relatively simple and common things I do with OC and see the looks on their faces, like when I told them that I had to make half a liter of chlorine gas (it was for a direct chlorination of an enol tautomer).
(As a side note about Breaking Bad, it bothered me that they focused so much on the acquisition of methylamine, but it was never really explained how they got such a huge quantity of phenylacetic acid precursors, since it's just as important as MeNH2. Just my two cents)

I'd say that the way I usually go about syntheses is that I find something interesting and then go for it. I mostly just follow my interests, I wish I had more of an interesting answer.




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[*] posted on 23-7-2016 at 14:01


I don't do any ochem (successfully, at least) at the moment, but my targets are usually unique but don't require any complicated materials. For example, the heterocycle "ethylene thiourea" requires very basic reagents to make. Same with citrazinic acid.



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[*] posted on 24-7-2016 at 12:06


Xeneficus, if you are wondering what to do next, I suggest you spend some time on YouTube or better yet: Woelen's site

I have a whole range of smelly experiments in mind. Both good smelling and some foul smelling :mad:

And as for the "usual" questions I get from other people "Do you make explosives" or "Can you make drugs" I usually have fun with the first group showing them pictures of the places I go to (Why would I make explosives when I can just pick them off the floor?) or toy with the second group using the DHMO joke.

Actually, I was having a bit of fun with a girl who had no scientific background back in June and telling her how bad DHMO was. Then I got a stern look and a "Hey wait, you think I'm an idiot?" She was actually listening and not thinking I was mad to have 10 liters of the stuff in my bathroom. We ended up doing biology experiments for some weeks :P
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[*] posted on 15-8-2016 at 13:21


Quote: Originally posted by Herr Haber  
Xeneficus, if you are wondering what to do next, I suggest you spend some time on YouTube or better yet: Woelen's site

I have a whole range of smelly experiments in mind. Both good smelling and some foul smelling :mad:

Good suggestion. youtube, surprisingly, has some good syntheses on it. Worth looking through, via YouTube accounts or keywords of some of the chemicals you have.




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[*] posted on 4-3-2017 at 11:40


Well I decide based on 3 things
Smell: Find something which smells nice then follow the yellow brick synthetic pathway to it
Color: Dye synthesis basically
Reaction: Just do the simplest/most classic example of fascinating reaction




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[*] posted on 4-3-2017 at 16:19


Well, I'm sure that they didn't want to make the meth-making look too easy on Breaking Bad... Adds to the entertainment value as well.

I choose my ochem projects using a combination of the methods described above- usually molecules that are colorful, good-smelling, or have an interesting structure. I also try to find things that I already have the materials for, and if I come across a new reagent that I can get cheaply, I'll look up what it's most commonly useful for (for instance, when I was able to get a large amount of 1-naphthol, I found that I could use it to make Martius yellow and a lot of other dyes). For satisfying OC, you'll probably need to spend a good amount of time (and possibly money) accumulating useful reagents, some of which you might not have an immediate use for. It's taken me a few years just to collect enough stuff to where I'm reasonably confident that I can do most of the OC at home that I'm interested in. Now it's just a matter of finding the time!

OC is definitely a very different animal than inorganic, but I think it is more rewarding and interesting once you get into it (you wouldn't catch me saying that a couple years ago). Also, I hate to say it, but it's hard to beat taking a couple semesters of OC at a university. Although you can certainly learn a lot from our friends on YouTube, a class will give you a structured outline of all of the types of reactions and why they work, which helps you apply it more generally and come up with ideas more easily. Reading through old OC textbooks can have a similar effect, but requires a little more personal accountability, since you'll be tempted to skip the boring parts and just try the preps.

It's kind of like taking cooking classes vs buying a few cookbooks and following the recipes. The latter is easier and more immediate, but if you go with the classes it's more rewarding in the long run and you'll internalize the information more.




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[*] posted on 4-3-2017 at 19:24


There are lots of non-illegal drugs worth making: aspirin, lidocaine, viagra, dariprim, and naproxyn have all been made as teaching exercises or to demonstrate a new technique or principle. Dyes are fun to play with, I remember making fluoroscein years ago and how fun it was. I later used similar work to make a tagged molecule for work. I have made luminol and some oxalate glow stick chemicals. And many esters smell great, the table of esters and what fruit they smell like is an awesome way to pick one to make, just see what fruit smell you want to create.

As for "Inorganic chemistry has the sex appeal of high energy materials", most high explosives used to be made from nitroaromatics, I got started in chemistry making a number of pyrotechnic mixtures and colored fire, which uses a good mix of inorganics as well as many organics.

And years ago when I had termites, I did some work to find out what chemicals were used, and was able to better understand what used to be used, what was currently being used and what was still coming, which allowed me to choose the best things available. But I certainly did not make my own termite agents, which would be not allowed by the EPA. But if you ever get termites, I can tell you want not to make... But I do miss chlordane. They say diamonds are forever, but chlordane is a close second, you could treat a foundation with it, and not have termites for 40-50 years minimum.
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[*] posted on 4-3-2017 at 20:45


I think Chem Player made a Grignard in an old wine bottle, just for giggles.



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[*] posted on 7-3-2017 at 15:47


If I'm going to make an organic compound, it will be a) an ester with an interesting smell, or b) something I can use as a ligand.



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8-3-2017 at 11:12
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[*] posted on 19-3-2017 at 20:36


There are also interesting neuroactive agents. Nootropics are particularly interesting. I started off with targeting 1-propionylation of piperazine selectively. And as an aside, discovered the opioidergic AP-237, 1-cinnamyl-1-(n)-butyrylpipiperazine. The propionamide, once alkylated with a cinnamyl group possesses some activity also.

Also some of this class are D2 antagonists, although I believe the (n)-butyramide, the strongest opioid of this class is not. I am extremely oversensitive to D2 antagonists. Can't even take domperidone, and that isn't even meant to cross the BBB much.

And theres interesting targets of all sorts in naturally occurring sources, and sometimes that can serve as inspiration, whereby to synthesize it rather than extract it from the biological source.

'odd' compounds too or compounds that stand out as bucking trends in a series are also good targets imo.
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[*] posted on 28-3-2017 at 17:25


Quote: Originally posted by Melgar  
I dunno, organic chemistry has had its own sex appeal ever since Breaking Bad became popular. Now I regularly have people ask me "do you know how to make meth as good as Walter White's in Breaking Bad?" Yes, it's an incredibly easy synthesis. In fact, Walter White was kind of an idiot for wasting so much energy trying to steal methylamine, when he could have just gotten nitromethane racing fuel by the bucket, and reduced it in a one-pot reductive amination. Also, what the fuck was that blue impurity? Nothing good, I'm sure.

Hell, tell most people that you can make methamphetamine by reductively aminating phenylacetone with methylamine, and they'll be impressed. "What's phenylacetone?" "Oh, you know acetone? Like nail polish remover? Like that, with a phenyl group attached to one side."

Note: do not actually make methamphetamine. Right now I'm actually trying to make dopamine via the Henry reaction, using caffeine as the base catalyst. None of it would be useful at all, but I'm not sure it's ever been done before and documented, and it seems a rather appropriate set of reactants.

[Edited on 7/23/16 by Melgar]


I'd like to hear how that dopamine went. I just made some caffeine (well, like .001 grams, but I will use caffeine pills instead of coffee), and might try that.
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[*] posted on 28-3-2017 at 17:26


Quote: Originally posted by DraconicAcid  
If I'm going to make an organic compound, it will be a) an ester with an interesting smell, or b) something I can use as a ligand.

Make cadaverine.
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[*] posted on 29-3-2017 at 09:55


The amount of times Tsath' has gotten the breaking bad themed comments, if he had a piece of lab equipment for every such remark made, by now he'd be making CERN worry about updating their setup so as not to fall behind :P
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